Sodium Hydroxide → 4-[3-(3,5-Bis(trifluoromethyl)phenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid

HRID 412430Notes

Reaction equation

HRID 412430 reaction equation
C[O:2][C:3](=[O:41])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C:29]2[CH:34]=[CH:33][C:32]([CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)=[CH:31][CH:30]=2)[C:12]([NH:14][C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=2)=[O:13])=[CH:6][CH:5]=1.[OH-].[Na+]>C(O)C>[F:22][C:21]([F:23])([F:24])[C:19]1[CH:20]=[C:15]([NH:14][C:12](=[O:13])[N:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:41])=[O:2])=[CH:5][CH:6]=2)[C:29]2[CH:30]=[CH:31][C:32]([CH:35]3[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]3)=[CH:33][CH:34]=2)[CH:16]=[C:17]([C:25]([F:27])([F:28])[F:26])[CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 865860584-[3-(3,5-Bis(trifluoromethyl)phenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid methyl ester

Product 1

HCID 223110784-[3-(3,5-Bis(trifluoromethyl)phenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[3-(3,5-Bis(trifluoromethyl)phenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid methyl ester (4.2 g, 7.36 mmol) was suspended in ethanol (80 mL) and added sodium hydroxide (4 N, 11 mL) and stirred at room temperature for 16 hours. The reaction mixture was concentrated to dryness in vacuo, and the residue was added water (50 mL) and acidified with hydrochloric acid (4 N, 12 mL). The aqueous phase was extracted twice with ethyl acetate (75 mL and 25 mL) and the combined organic phases were washed with water (3×15 mL), dried (magnesium sulphate) and concentrated in vacuo to afford 4-[3-(3,5-bis(trifluoromethyl)-phenyl)-1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness in vacuo
  2. additionthe residue was added water (50 mL)
  3. extractionThe aqueous phase was extracted twice with ethyl acetate (75 mL and 25 mL)
  4. washthe combined organic phases were washed with water (3×15 mL)
  5. dry with materialdried (magnesium sulphate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19903746d3bb4810a1208cdfec4a2961
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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